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Vocabulary Practice

Could you please correct the follwoing sentences?
1. You'd better contemplate building such a large house as you may find it difficult to secure it (Do you normally use more than one "it" in one sentence?)

2.The mention of Peter's name was too dreadful to contemplate.

3. Are you prepared to contemplate being sacked?

4.Jack is seriously contemplating studying abroad.

5. The pain in his leg was so excruciating that he even started groaning hoping that it would ease that unbearable pain.

6. While describing the events which took place in the period of 1941-1942, the historian asked the audience to remember that it was a year of excruciating terror.

7. He was terribly upset by forgetting to wind up his watch.

8. I don't think you should have taken it seriously. They were just winding you up!

9. The teacher asked the class not to wind up Max, a newcomer, who had been trasferred to their school two days previously.

Re: Vocabulary Practice

1. You'd better contemplate building such a large house as you may find it difficult to secure it
This sentence doesn't work for me; the meaning isn't clear. I also think the second 'it' is wrong. Is this what you meant?:

You'd better think about building the house as you may find it difficult to find such a large one.